To Brooklyn or Bust
by upchitzcreek
Summary: Dan and Blair related. Set after they graduate high school and shortly enter NYU.
1. Chapter 1

Blair's eyes scanned her closet as she decided what to wear. She always had to be the best dressed at school. She slid her fingers against a few sweaters as if she was feeling for mistakes. She picked up a black headband with a small off centered bow. She pushed it through her hair and gave a smile in the mirror. Another perfect outfit for Miss Blair.

She arrived at school and listened to her minons as they gabbed on. They always worried about the stupidest things. Everything in life wasn't about having a man on you arm it was about how you carried yourself. Blair felt as if they were just holding her back. Yale would be the perfect escape. Away from all these single minded people and on to better things.

"Hey B!" Serena greeted Blair with a smile.

"S, you look.....presentable." Blair almost choked on her words.

"I'm actually not staying in school today. Just dropping of my paper then leaving to have my birthday shopping spree with my mom."

"Your birthday isn't until Saturday. Plus shouldn't you be getting prom stuff together, its next week."

"Well my mom and Bart are attending a party in Paris. Bart's new hotel opened up. My dress is already picked out, I'd never wait until the week before." Serena began to sulk.

"At least your mom cares enough." Blair played with her food. Her mom didn't even notice when she left the house. Unless Eleanor needed her Blair felt unloved.

"Well I should head off. Don't forget to get my gift." Serena stuck her tongue out at Blair.

Just as Blair was about to speak Dan sat down. She gave him this odd look. In her head she was screaming for him to get up and leave. The last thing she needed was a Humphrey moral story of the day. He was like a bad tv show that was stuck on reruns in her head.

"And what do I owe this pleasure?" Blair snapped.

"I need your help with a gift for Serena. We just got back together and I need the perfect gift." Dan was starting to plead. He couldn't even believe that he was asking Blair for help.

"Listen, I'm not totally on board yet with the Dan and Serena love train. I'm waiting on the crash and burn." Blair always gave out her sarcastic comments with a smile. She always felt that a smile always masked how you really felt.

"Blair, I'm not willing to beg. Can't you help your best friend's boyfriend?"

Blair bit her lip as she looked in disgust towards Dan. She didn't believe he deserved a second chance with Serena so soon. Nothing she would ever say would prove as the voice of reason for Serena. She sort of envied their commitment. She'd grin and bear this horrible experience for Serena's sake.

"I'm feeling in a charity giving mood." Blair broke the silence. "Meet me at this address and I'll take you to her favorite stores."

Blair walked off and left Dan with a confused look on his face. She laughed as she looked back to confuse him even more.

Dan met Blair at this fancy boutique. She was an hour late. He figured she got a facial or something. Anything to prolong spending time with him. She made him feel like a piece of did Serena have to be best friends with the devil? She finally arrived. She didn't even acknowledge he was there. She walked straight into the store and started throwing clothes at him.

"I can't afford any of this stuff Blair!" Dan looked at the price tag on the Dior shirt.

"Well you should have thought about that before you dated a rich girl." Blair sat there trying on sun glasses.

"I asked for your help for a meaningful gift. I don't want to get her something she can get herself any old day." Dan put down the stack of shirts Blair handed him. He just shook his head.

"Listen Humback, I don't do meaningful. But if you want I'll...go to Brooklyn with you." It pained Blair to say the words Brooklyn. She felt as if it was a sewer compared to the UES.

"I don't want your pity Blair."

"No, Dumphrey I'll do it for Serena.

"I'll ingore the name calling."

Before they even stepped foot into the store it began to rain. There was thunder and lightning and the rain came pouring down. Blair cover her face with her bag, hoping the water would stay out of her eyes. She was just frozen there. Dan grabbed Blair by the hand and started running. His loft was three blocks away. Blair relentless ran with him. They finally reached his loft and went inside. Dan's keys kept slipping through his hands. He finally managed to get the door unlocked.

"The storm is getting worse outside Blair you'll have to stay here."

"In Brooklyn?"

"You make it sound like the forgotten city." Dan replied as he quickly grabbed towels from the closet.

Blair squeezed all the water out of her hair and into the towel. "You'll be getting my dry cleaning bill."

"Of course I will because I control the weather now." Dan rolled his eyes. "The worst part of it all was I have no gift for Serena."

"I get you something simple Humphrey." Blair knew she was doing him a favor.

"I don't take handouts."

"It's a thank you, for putting me up in this shack."

Dan wanted to reply but he just didn't want to go down to her level. He pulled out the couch and made up a bed for Blair. He knew she'd find a million things wrong. The pillows weren't fluffed or the sheets were ugly. He just wanted to go to bed. When he was done, Dan stood back and looked at Blair. She was looking through a photo album.

"Your bed is done your highness." Dan motioned to the couch.

"You know my mom hasn't even called to see if I'm alive or not. Your family has a million of these albums. I don't even think I have one."

"Thats impossible. Your mother must have kept some."

"Of her models, but not me." Blair was fascinated with each paged turned. She was actually jealous. Even envious. Feeling pathetic Blair broke the silence. "I need my beauty rest."

"Oh Blair one more thing. I tend to sleepwalk."

"Well you can sleepwalk into a wall then." Blair replied pulling the covers up to her shoulder.

"And I sleep naked."

"Humphrey!!! Ew!!!!!! Your an ass."

Dan laughed as he walked into his room and Blair pretended to gag.

When Dan awoke Blair was already packed and sitting on his couch. She had folded up the sheets and put them away. Dan was shocked that Blair actually did some work. He scratched his head try to figure out if this was all a dream or something.

"This doesn't change anything."

"What?" Dan grew confused.

"You housing me for the night. This doesn't mean I'll be nicer to you."

"I wouldn't want you to. Blair Waldorf doesn't play nice."

Blair picked up her bags and walked out of the loft. She'd never tell a soul what happened last night. If Dan spoke a word she'd deny it. She'd make sure no one would believe him. Part of her knew Dan wouldn't tell. He upheld this honor. Plus if he wanted Serena to get a great gift, he'd be nice. She knew exactly what to get Serena from Dan.


	2. Chapter 2

**A/N: I tried to make it as sarcastic as possible, I tried! Hope you all like it =)**

* * *

Blair walked into the room like she owned it. Even though it was prom, all eyes were on her. Could it have been that her dress was the best, or that she walked in solo? The lights gleamed into her eyes as if she was a movie star. The decorations that she had picked out were all put up perfectly. The flowers were arranged just the way she had demanded. This was her prom. If anyone complained she would give them this look that made them back down. Who would dare to go against Blair Waldorf?

"B!" Serena shrieked. "You look great."

"That was my goal." Blair said sarcastically. "So, you finally dumped Dan?"

"No, he's getting us drinks."

"Well, whatever."

"Where's your date?" Serena hesitated before asking.

"I decided no guy was worthy enough to take me." Blair had her better than everyone else tone.

"Do you want me to hang around?"

"No, I'll steal some guy away from his date. It will be the end to a perfect night."

"Someone else's misery always is for you." Serena replied as she walked towards Dan.

Blair didn't want pity. To have Dan and Serena hanging all over her all night, the thought killed her. To be treated like a child that had to be watched. Somehow she had to make the night about her again. She could play one of her games with Chuck. But even that got boring after awhile. She could make Nelly cry or feel bad, but she did that yesterday.

The night dragged on. Blair found ways to amuse herself but she was really waiting to see who would be Prom King. She was shoe in for Queen. She hoped it was Nate. They would make the perfect couple, plus it would stick it to Chuck. I mean they were picture perfect, and Nate was well liked. She would even get a spotlight dance with him. It was the perfect moment.

"Excuse me. Can I have everyone's attention." The teacher exclaimed.

"This should be good." Blair whispered. She found her way next to Nate and Serena.

"I will announce the new Queen and King of the Prom." The teacher carefully ripped the card open. "Queen is Blair Waldorf."

Everyone clapped. Blair put on her surprised face, as if she had no idea she would ever win. She place the crown on her head, as if it was meant to be there all along.

"And Prom King is......Dan Humphrey."

"What!?" Blair screamed. "Is this some cruel joke against humanity?"

She tore the card from the teacher's hand. She looked out at him in the crowd. What kind of sick joke was this? Who would ever vote for him? She had a million questions running through her mind.

Dan made his way up the stage steps. He had a nervous look on his face. He placed the crown on his head and looked uncomfortable. He was wondering the same thing as Blair. Why did people have to put him through this torture. Now he would have to dance with Blair and take a few pictures for yearbook. Blair was more worried about Gossip Girl headlines and people mocking her.

"Now for the spotlight dance."

"If you think I'm touching him, your wrong lady." Blair snapped.

"Well you did sleep at my house and mock me for a whole day, so this is God's payback."

Blair looked at him with angry devil eyes. "This has to be a mix up! No one even likes him!"

"Ouch!" Dan put his hand against his chest. "Blair lets just get this over with."

"Listen Dumphrey, I have an image to uphold."

"Is Blair afraid? I promise I had my cootie shot."

"Sarcasm, really?"

"Blair look you're making a scene, lets just do this."

Dan extended his hand out towards Blair. She reluctantly took it. They walked out on to the middle of the dance floor. She tried to place her arms conviently for her. They swayed to the music. They both looked so bored. They felt that they song lasted forever.

"Sorry that you're put through this hell." Dan broke the silence.

"Just a practical joke. I feel bad for you. Thinking people actually like you."

"You don't hold anything back to do."

"Just because everyone loves me, and tolerates you, it makes me bitchy?"

"No, you have to be born a bitch." Dan smirked. "What did you ever get Serena? She just told me she loved my gift."

"Well Cabbage Patch, I got a copy of your story bound it and put of picture of you two I stole from her room. With some roses of course. It totally screams, pathetic."

"That was nice of you."

"I had to make it seem like you did it, I mean money was a factor."

"And I will pay you back Blair."

"Lets just call it even."

The music stopped and Blair broke her hold over Dan.

"Is my boyfriend safe?" Serena jumped in.

"For one night, I left him unharmed."

"Yea, she put on a happy face and pretended that I was street trash."

"Don't worry, I'll be taking a three hour shower just scrubbing my hands alone." Blair rolled her eyes.

"Lets go Dan. Night B." Serena hugged Blair goodbye.

"Night Blair." Dan semi smiled.

Blair didn't respond. She just watched them walk off.

"So is Blair Waldorf gonna move into Brooklyn?" Chuck snuck up behind her whispering in her ear.

"And mix with Dan Humphrey and company, no way."

"Then my joke had no affect over you. Did you really believe people would vote for him. He's lucky people know his name."

"You're just jealous. He got two girls tonight and you'll be going home alone." Blair pushed Chuck off her. "Chuck Bass' Hotel Room, Party of one."


	3. Chapter 3

Blair sat there at the bar twirling her straw. The bartenders tried to hit on her and normally she find this as a sport but she just wasn't in the mood. Dorota had to visit her sick brother, Chuck and Nate were away, and Serena would be leaving for the whole summer. She truly felt all alone. She always counted on one of them being there just for her to have someone to bother. There would be no schemes, no boys, no fun. No purpose for her summer. She would have to find something else to do or wrap herself up in a charity or some club. Or she could always visit her dad. Then she always felt like the third wheel to her dad and Roman.

She downed the drink. Before getting up she saw Dan out of the corner of her eye.

"Humphrey, I'm not in the mood."

"Serena wanted me to let you know, she got to the airport fine and she'll call you."

"Messenger boy now?"

"Whatever. I'll let you finish or get back to what you were doing."

"Why don't you sit." Blair felt weak after she said that.

"Um, is that a good idea?" Dan replied in a confused manner.

"You have nothing to do and I have no one to be with so we might as well drown our sorrows."

So they drank and spilled their guts. They both realized that they would be too drunk to remember what the other said. They talked about living up to standards and not being enough for their parents. Dan talked about college and how he couldn't afford anything. Blair just looked at him blankly. She didn't know if she actually cared or she had some great buzz. Dan stopped drinking at one point while Blair kept pouring them down.

"I think that's enough Blair."

"It's never enough. I'm never enough." Blair began to sob.

"Let me take you home."

Dan wrapped Blair's arm around him and pick her up from her seat. He threw some money on the counter and picked up her bags. The bartender nodded at him. He got her into the car and started to walk away.

Blair leaned out of the window. "Don't you need a ride?"

"I'll walk."

"But what if I don't go directly home? How can you make sure?"

"Blair I'm not playing games."

"This isn't a game, just a ride. Do you really want my disappearance on your hands?"

* * *

_Spotted: Lonely Boy and B getting into a limo together. Did hell finally freeze over? Or did B want a side of Dan with her fries?_

_xoxo,_

_Gossip Girl_

* * *

Dan sighed and reluctantly got into the car. The whole ride was silent. Blair was starting to sober up fully and Dan just kept looking out the window. Blair didn't know if she should make small talk or continue with this whole "we're nothing more than two people in a car together."

"Who knew I could play nice right?"

"You were just lonely."

"I'm always lonely."

"You put up a good act." Dan replied and went back to looking at trees.

Dan looked at Blair and sighed. He opened the door and walked behind her. He made sure she got into her house. He did a take around the down stairs area to see if anyone was home. He didn't want to leave he and hated that he actually cared if something happened to her. He was so kind and caring, even to someone who hated his guts.

"Well, everything looks fine."

"I hate saying this, but thank you." Blair scrunched her face.

"You're my girlfriend's best friend."

"Yea, but we hate each other." Blair did a small laugh.

"You may hate me but I respect you, in a way."

Blair led Dan towards the door. She flung it open and put her hand on the wall. Dan turned to say goodbye and there was an awkward closeness. Blair leaned in and kissed him. It was about a five second kiss. When they pulled away, Dan touched his lips and walked away. Blair slammed the door and fell to the floor. She was shaking. What had she done? She just kissed a Humphrey! A kid from no man's land Brooklyn, who liked to read weird books and dripped whit sarcasm.

Blair picked up her phone and dialed Dan. "Hi it's me. Um about that contact we had, forget it happened. If anyone ever found out about it, I'd die. Plus S would laugh and never let you live it down. It's for the best. Call me or don't." She quickly hung up.

Call me? That made her sound desperate. She hated how everything was in Dan's corner now.

"Miss Blair I am home." Dorota said cheerfully.

"It's all your fault!"

"What did I do?"

"Because you weren't here I had to rely on Humphrey and we kissed." Blair grew angry. "I left him a voicemail. This is unheard of!"

Blair stormed out of the hallway and into her room. She slammed the door and fell into her bed. She hugged her pillow and tried to get thoughts of Dan out of her head.


	4. Chapter 4

Blair waited by her phone to see if Dan would call. She felt like one of those hopeless losers who waited for their boyfriend to call. Only Dan wasn't her boyfriend, he was this scab that she wanted out of her life. She had Dorota follow him around to make sure that Dan didn't tell a soul. She kept reading the Gossip Girl post on them. And how they were spotted, together. The worst thing ever, even worse then the kiss. Other people saw them together. Of course she told people they were just talking about Serena and that he never really got in her limo.

"Why am I letting Brooklyn rule my life?" Blair sighed.

"I don't know, you tell me." Chuck echoed into the room.

"What are you doing here."

"You never called back, I was worried."

"Aren't you suppose to be screwing half of Italy by now."

"Don't do the act, Blair, we both know you don't give a shit who I do, as long as I come back to you."

"I have seen the light. I realized, I'm no one's second place." Blair glared as she pushed Chuck away.

Just before Chuck could make a move on Blair, Dorota walked in. She placed her things in the closet and told Chuck to leave. She made up an excuse saying Blair had a dress fitting for Eleanor's show.

"What took you so long?" Blair screamed.

"Miss Blair, Dan is nice boy he no tell your secret."

"And how would you know?"

"He saw me following, we talk."

"I'm glad you were having tea time with Humphrey, while I was going insane."

"He come by later to talk things out."

Blair looked at Dorota as if she did something unspeakable. Like she had invited a homeless man or the devil himself over. Blair opened her mouth to say something but she refrained.

She simply smiled and blurted out. "I guess I'll find something to wear then."

As Blair scanned through her closet she flashed back to the kiss. She wished it actually went better. She hoped that Dan may have felt something, and she knew it was stupid to think that since he was going out with her best friend. She hates awkward moments and the aftermath. She felt as if she traveled from one awkward moment to the next. She slipped on her dress and zippered up the back.

"Miss Blair, he's here."

Blair glided the headband through the hair as she took one more peek in the mirror. She put her hand on the banister and descended down the steps.

"Hi." Blair said in a coy manner.

"Hey. You look nice."

Nice? Really? Blair thought.

"Thanks. You look clean."

"It was my month to shower. So I thought, why the hell not?"

Blair smiled. "About the other night."

"It was fine. You never meant for it."

"But what if I did?"

"Blair Waldorf wanting me? A low commoner?."

"Stop."

"I'd bet you'd scrub your face off. Or if we did it, you'd burn the sheets."

"More like give the bed away to good will."

They both laughed.

"There's the Blair I know."

They sat down and just talked. They completely let their guard down to each other. Blair, mostly cause no one else knew of this. No one would ever think Dan was at her house.

"Maybe you should getting going. You'd hate to be seen here."

"Or you'd hate it."

"I actually learned to stop caring what others think."

"Well that's good."

Before Blair and Dan could finish, Eleanor and Cyrus came in. They didn't even notice them. They started yelling at each other and Eleanor threw a vase. They kept going on and on, Blair went by to caring to what others thought, mostly Dan. Cyrus ran upstairs and slammed a door. Eleanor gazed at Dan. She got up real close to him and with a threating look grabbed Blair by the arm.

"Take your friend somewhere else."

Eleanor walked off as Blair wipped a tear away.

"I'm not leaving."

"Now is not the time to be noble."

"Then you are coming home with me."

"I'm still recovering from Brooklyn round one."

"Don't fight me, let me stay."

"Fine but you get the floor."

"Aw! No snuggling?"

Blair slapped him and laughed. They both ran upstairs and quickly shut the door behind them.


	5. Chapter 5

**AN: Ah! I know I am a horrible person for not updating it (I kinda forgot about it once school hit) It's been like a year already and I apologize to all of you that read it. Hopefully you'll continue even though i was a very bad girl! So, given s3 and all it's wonderfulness I've made some changes. I left it off where it was a week after graduation and it was the summer. Now, lets speed up time a bit so it's a week before school at NYU. This way I can incorporate some of what happened into the fic. Again really sorry about all of this. Italics are thoughts.  
**

* * *

Blair awoke to an empty bed. She had set Dan up on the floor, but was surprised that he had remained there the entire night. She expected, just like any other guy, he'd try to make his way onto her bed and try something. _Guess Humphrey is more honorable_. She rubbed her eyes and pushed her curls away from her face. She wanted to see if she was home alone so she could get Dan out of the house fast. She slowly placed her feet on the floor and tried to tip toe out of the room without Dan waking up.

"Blair?" Dan said in a groggy voice."

"Yeah?" Blair was shocked it woke up so easy.

"I was waiting for you to wake up."

"With your eyes closed?" The snark was deep in her voice. "Listen Humphrey, you didn't have to stay the whole night."

"But what if you woke up and I wasn't here." He was finally fully awake.

"I would jump up and down with joy." Blair gave a half smile.

"Really? Even though you spent half the night telling me all about your parent problems and your insecurities." Dan fought back.

"If you tell anyone I'll deny it. Plus I'll tell everyone about Cedric." Blair always had the upper hand.

"Gotcha. I'll go."

"I'm surprised you actually slept on the floor all night."

"You mean sneak into your bed?" Dan replied putting on his jacket.

"It's been done before." Blair folded her arms.

"But that would be invading your space. Plus you'd beat me with a headband or something."

"I'd have to burn the sheets too." Blair laughed.

"See, so it helps I stayed away. Well I have to go get books for NYU, so I'll see you around."

"I'll walk you out. After all, you were a guest in my house."

"Or you want to make sure no one sees me?"

"Either would be just fine."

Dan looked blankly at her.

"What? Creeping me out Humphrey."

"Nothing, just thought maybe you'd finally stopped caring what others think, like you said the other night."

"It's not what people think of me, it's who they expect me to be. And..."

Before Blair could finish Eleanor tore into her room. She gave an evil look to Blair once she saw Dan. She walked up to Blair and got close to her face.

"I'm not harboring any of your boyfriends."

"Me? No, no....I...I'm not."

"He is a guest mother. He's my friend."

"Well whatever he is, get him out and we shall talk about this later."

* * *

After ten minutes of begging, Blair convinced Dan to let her go with him to the bookstore. She needed to get out of the house and away from her mother. Dan's eyes scaled shelves and shelves of books to find his journalism textbook. Blair basically stood there looking at air till he was done. He finally found it after a twenty minute search. Blair stamped her foot the entire line to the register. She rolled her eyes at the cashier with her cotton blend hippie shirt and his brown pants. As they walked down the street they saw Vanessa.

"Hey V!" Dan exclaimed.

"Why are you with her."

"I'm good thanks." Dan mocked.

"No seriously, you two hate each other."

"Hate is a strong word."

"Look Vanessa, you're just jealous that everyone eventually drops you. First Nate, now Dan."

"Blair, calm down."

"No, she comes in here acting like it's the end of the world."

"Or hell freezing over." Vanessa interjected.

"Both of you calm down. Yes, Vanessa I was with Blair. No, it's not the way you think and it does seem crazy. We're all gonna be in the same college in a week. Let's not make this like high school."

"Whatever Dan, when you come to your senses, you can call me."

Vanessa walked off and Blair smiled as if she did nothing wrong. They started walking to the car and it felt like an eternity. Dan mostly stared at the window while Blair was staring at him. _What is wrong with me? Why do I care that he's mad? Normally that would make me happy. _The driver stopped the car and Dan walked Blair in. Eleanor was waiting for her by the elevator.

"I thought I told you to get rid of him."

"He was just walking me in."

"I don't need this right now. My fashion line is crumbling as is my marriage. Then there is you...."

"Blair, can I talk to your mother?"

Dan motioned for Blair to go in the elevator and Eleanor steamed. No one, and I mean no one interrupts a Waldorf. Once Blair was out of sight Dan started speaking.

"Look, I know I have no authority here and you probably won't listen to anything I have to say, but you're daughter is begging for attention her. All she wants is to make you happy and you only see faults. The biggest fault Blair has, is having a controlling mom like you. Blair can be rude, selfish, ignorant, petty, and will step on anyone she has to. But she is also caring, smart, witty, and would do anything for the people in her life. If you continue to push her away you will never know the person you're daughter is, or you'll make her a worse version of you."

As soon as Dan finished he left. He didn't stick around to see Eleanor's reaction. He wanted to bolt before she started screaming or punching. Blair crept from out of the corner and looked at her mom. Eleanor began to cry and mouthed the word sorry. She hugged Blair and petted her hair. Blair was shocked that one kid, a kid from Brooklyn, could tear so deep into her mom that she broke down.

_Maybe I underestimated Humphrey. Maybe he is a friend._

_

* * *

  
_

**AN: Yeah I know I made Eleanor totally bitchy to Blair but that's how I left it off last time so I had to keep up with it. Next chapter will be an overview of the DB interactions in s3. Then I will move forward from there. Hope you all enjoyed it :D**_  
_


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